yellowish-red azo dyestuffs and process of making same



iiniso STATES PATENT OFFICE.

L WAGNER, OF SODEN, AND ALBERT FUNKE, OI HOGEST-ON-THE-m, GER- ASSIGNGES TO GBASBELLI DYESTUFF OOBPOBATIOIF, 0] NEW 103K, I. Y.,

GUEEQMTIQIT.

'iIISLTwTZiSWIBH-BED AZ O DYESTUII'S AND PROCESS OI MING SAME.

33c Brewing.

ii e have found that new azo dyestuffs giving valuable yellowish-red tints and the lakes of which are of great fastness to light can be obtained if 3-nitro-4-diazo-1-pheno 6 others, especially the ethylor methylethers, are combined with an aceto-ac'etic acid anilide which is substituted either by an alkyl group'- in ortho position to the amino group, or by an alkyloxy group in para 1 position to an amino group. In the first piece the aceto-e'cetic acid ortho-toluidide,-

the perennisidides or para-phenetidides or their homologues or substitution products me he pructicull used.

ur invention 18 illustrated by the following examples, the parts being by weight: (1) 18.2 parts of 3-nitro--1amino-1-phenol ethyl ether are diazotized and the solution of the diazo compound is run into an aqueons suspension of 20 parts of aceto-acetio acid ortho-toluidide to which has been'added the required quantity of sodium acetate in order to tscilitste the reaction. I I The coupling process is finished at once. The separated and dried (lyestufi is a yellowish-red powder.

(2) The diazo solution of 18.2 parts of 3-iitr04-tli11lil0-l-Ph8HOl ethyl ether is run into anegueous suspension. of 21.5 arts of aceto-nc-etic para-snisidide to which has been added the required quantity of sodium acetate in order to facilitate the reaction.' The formation of the dyestufi proceeds quickly and is immediate y complete. In this Way a yellowish-red dyestufi is obtained.

{3} The diezo solution 0516.8 parts of coupled with an sikeline solution of 20 parts ofeo-sto-scetic ortho-toluidide in presence of o i dyestuii is filtered oil by suction and d in the iEGTLL of a paste or a powder.

o claim:

Application filed October 8, 1925. 861181 10. 61,301.

1. The process of producing yellowishred a-z o dyestuffs, which consists in coupling a 3-n1tr0-4-diazo-1- henol-al 1 other with an aoeto-acetic anili e of the ollowing composition:"

on, d- -o Lula:

wherein R stands .for an ortho-alkylanilide residue or a para-alkyloxy anilide residue.

2. As new products,

v azo dyestufis of the following composition:

stills, l iQ- being, when dry, a yellowish-red powdor,. dissolving in sulfuric acid- -to a reddish-yellow solution.

In testimony whereof," we afiix our sigi m HERMAN WAGNER.-

Du. ALBERT FUNKE. 

